Water → HCID 68683629, compound

HRID 1713801Notes

Reaction equation

HRID 1713801 reaction equation
Cl[C:2](=[O:7])[C:3]([O:5][CH3:6])=[O:4].Cl.[O:9]([CH2:16][CH2:17][CH2:18][NH2:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1C=CC=CC=1.O>C(Cl)Cl>[O:7]=[C:2]([NH:19][CH2:18][CH2:17][CH2:16][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 79846Methyl chloroglyoxylateHCID 18590545(3-Aminopropoxy)benzene hydrochloride

Product 1

HCID 68683629HCID 68683629, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl chloro(oxo)acetate (1.77 mL) was added to a stirred solution of (3-phenoxypropyl)amine hydrochloride (3000 mg) and pyridine (2.98 mL) in DCM (100 mL) at 0° C. After the addition was complete the solution was allowed to warm to ambient temperature and stirred for 16 hours. Water (50 mL) was added and the mixture was extracted with DCM (2×75 mL). The organic extracts were combined, washed with brine (50 mL), dried and concentrated in vacuo to give an oil. This was purified by flash chromatography on a 90 g Biotage™ silica column using a gradient of 10-60% EtOAc in hexane as the eluent to give methyl oxo[(3-phenoxypropyl)amino]acetate (3212 mg) as a solid; 1H NMR δ (CDCl3) 7.60 (1H, bs), 7.28 (2H+CHCl3, m), 6.94 (3H, m), 4.07 (2H, t), 3.90 (3H, s), 3.58 (2H, quartet), 2.08 (2H, m), +0.1 mole of EtOAc; MS m/e MH+ 238.

Workup

  1. additionAfter the addition
  2. extractionthe mixture was extracted with DCM (2×75 mL)
  3. washwashed with brine (50 mL)
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto give an oil
  7. customThis was purified by flash chromatography on a 90 g Biotage™ silica column

Sources & evidence

ORD record
ord-a662f939efc54032a8cc040008ab7831
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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